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So! I have done:

Jiyel Scholar
Romanced Ana.
She was really wishy washy because I had no idea what I was doing. Low courage and self defense, luckily Ana didn't mind.

Hise Pirate
Romanced Emmet, Claremont, and Ria
Blunt, noble, brave, good self defense. Always took the "nice to servants" options.
Still hadn't read a walkthrough or anything so I'm pretty proud of myself for managing 3 romances :D (not concurrently, but I didn't have to replay very much) Couldn't ever get Emmet's week 3 date to succeed though for some reason.

Revaire Widow
Romanced nobody. No friends.
Evil and manipulative. My aims were to romance some of the nastier characters (no luck) and see if I could alienate Ana (yes!) It was kind of fun being so awful and watching her fail.

This is the point where I started reading a walkthrough.

Wellen Tomboy
Romanced Hamin
Maximised Charm, Courage, Street Smart

Failed at making an Arland character several times.

Corval court lady
Romanced Ana because nobody else liked me :(
Tried to maximise likeability, Eloquence, Persuasion, flora and fauna, politics to romance Lilse and/or Zarad. Got Penelope's full friendship which is something.

Jiyel scholar #2
romanced Lyon
Maximised book smarts, intelligence, nobility

Revaire Widow #2
Romanced nobody, dammit (though Ana was willing)
Completed Cordelia's friendship and possibly Avalie's (succeeded at her first week event, at any rate) Perfect Orvu game, woo.
Maximised Interpersonal Insight, Courage, Quick Wits, unethical to romance Gisette but failed ;_;

New ones after making this post:

Arland princess
Romanced Emmet and Hamin
Started out a fluffy passive ball of nice, I boosted her nature and courage as the game went on.

Corval lady
Romanced Gisette
Manipulation and interpersonal insight up the wazoo.
The mistake I was making before was using a Revaire widow, the way the dialogue plays out I think that origin may be IMPOSSIBLE to romance her with. Wish I'd upped my insight more during introductions, would have suited the character. Didn't have to be unethical, but have to wonder why an ethical person would date her.

Revaire Widow
Romanced Zarad AT LAST
Also got all the secrets.
Setup questions:
1.Under your spell
2. -
3. political
4. bribed
5. Quickly
6: Things no proper lady would know
7. talk
8. -
9. intelligent
10. -
11. suggest
12. politics
13. -
Weakness: grace
And then I got max insight during the introductions and spent the rest of my time raising the following stats and doing all the castle explorations.
Week one: 25 street smart 150 interpersonal insight, 180 persuasion (ball room)
Week 2: 175 likeability, 125 quick wit, 50 intelligence
Week 3: 300 persuasion (ball room ) 100 book smarts (music room) 150 interpersonal, 150 quick wit
I did any personal invites that came along that would raise relevant stats, this meant I ended up romancing Hamin and Zarad and got the dual thorns achievement hurrah. I also got asked out by Jarrod for the first time thought that fell flat quickly.
My name was Lady Sneakly which was amusing.
Failed to romance Jasper and I can't tell why ;_;

Corval lady
Romanced Jarrod and Woodly
Interpersonal Insight, manipulation, persuasion, and some courage, max insight, saw all Woodly's secret scenes
Hahaha omg these guys are so terrible, I can't believe I dumped Zarad for them (yes I got him AGAIN without even TRYING) Props to the game for making Jarrod so uncompromisingly awful with no ~hidden depths~.

Jiyel Scholar
Romanced Jasper
Maxed out quick thinking until the week 2 Forbidden Quarter scene, super nice to servants, visited my room every week, compromised on my Harmin date, invited servants to events.

Lady Qwerty of Jiyel
Fell off a cliff
Chose the first option every time unless there was another option to skip content. Somehow passed my introduction haha.

Hise pirate
"Romanced" Lisle AW YEAH
Also won the boat race and impressed the matchmaker, woo
Was as likeable as possible, maxed Eloquence and beauty until they were super high then evened myself out with etiquette, charm and academics. Invited the siblings to a musicale, a boat race, and a midnight picnic. Gave them the perfect presents. Got me a cute gay husband aw yiss. Also a cute maid girlfriend, I assume she actually got dumped when I chose Lilse but the demo doesn't show it so it isn't my canon. Hopefully there will actually be some way to marry Lilse and romance Ria (or Gisette/Woodly assuming someone could get along with both haha) even if game mechanics mean you can only see one path.

Remaining aims: ALL DONE
~~Arland character~~
~~Emmet date week 3~~, ~~romance Gisette~~, ~~Zarad~~, ~~Woodly~~, ~~Jasper~~, ~~Lisle~~, ~~Jarrod~~ (he's so awful this is a low priority)
Other interesting looking achievements: ~~die~~ (I have avoided challenge mode thus far but will give it a shot for this ;)), ~~figure out who's trying to assassinate me~~

I can NEVER seem to succeed at Zarad's date. I've yet to make it my to priority though. EDIT: Done! AND I WASN'T EVEN TRYING THAT TIME.

I liked all the romances I've done. Claremont's started well but didn't quite click with my characters. Lyon and Ana are pure catnip for me so I can't judge objectively, but I think Ana was better. Hamin's not my usual type but the relationship with a tomboy was a sweet match. Avalie is great, very sad she and Penelope aren't romanceable. Meanwhile I felt weird romancing Ria, she's nice but the power imbalance is huge, though it felt less weird as a thing I stumbled into by accident because my character was just that nice. EDIT: Arland Princess/Emmet works really well since they know each other already. Jarrod and Woodly are terrible but amusingly so.

The backgrounds are nicely varied. It's hard to say what I think of the plots without knowing how they play out, but they are all interesting. I'm especially worried for my poor Jiyel scholars!